When Your Calendar Files a Restraining Order

Scheduling Drama Part I

July 25, 20252 min read

When Your Calendar Files a Restraining Order

Your schedule might look like a color-coded oasis, but really? It’s a chaotic jungle full of surprise snakes, fire drills, and interpretive dance-level flexibility. Let’s revisit the real stars of your booking mayhem:

  1. The Eternal Email Thread “How about 2 PM?” “Ooh, maybe 3?” “Actually, could we do 4:15?” …and now your inbox is holding a hostage negotiation with someone trying to book a massage.

  2. Odd-Hour Obsession “Is 6:07 AM okay?” They ask, fully convinced their back pain operates on lunar cycles. You start scheduling appointments by sundial just to keep up.

  3. Multi-Channel Mayhem They book online, reschedule via carrier pigeon, confirm with an Instagram meme, then call your mom. Every platform except the one where it’s supposed to live.

  4. App Apocalypse Your scheduling software glitches and deletes your entire day. You stare into the void, whispering affirmations to your Wi-Fi like it's a plant.

  5. Phantom Booking Showdown You walk in, expecting your 2 PM… but there’s nobody. You check your app, and it still says 2 PM. Did they cancel telepathically? Is there a wormhole in your software? You stand there staring at the massage table like it’s going to explain itself. Plot twist: they booked for next Tuesday and showed up with a full-blown gratitude letter and a playlist they made for the session.

  6. Session-Length Smackdown “It says 90 minutes, but that includes, like, breathing, right?” They try to lobby for another half-hour like it’s bonus content on a DVD.

  7. Reschedule Roulette Their appointment moves so often your calendar looks like it’s auditioning for Cirque du Soleil. One misplaced drag and the whole thing somersaults into chaos.

  8. Deposit Dithering “What if my dog gets sick?” “What if Mercury’s in retrograde?” Suddenly your $20 deposit is being interrogated like it owes them money.

  9. Waitlist Showdown You post a cancellation and seconds later get two texts, one DM, and a smoke signal. You decide who gets it based on who’s brought snacks before.

  10. Treatment Switcheroo They booked a Swedish massage, walk in like, “Today feels… volcanic. Can we do hot stones, deep tissue, cupping and maybe a nap?” You look at your supplies like you’re prepping for a spa-themed episode of Survivor.

Got a scheduling drama that deserves its own theme song? Help us with Scheduling Drama Part 2!  Email us your anonymous tale of chaos at [email protected] and let’s turn your calendar catastrophe into comedy gold.


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